Compound Detail
CHEMBL448
PENTOBARBITAL 💊 Approved Drug
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💊 Approved Drug
Basic Information
| ChEMBL ID | CHEMBL448 |
| Name | PENTOBARBITAL |
| Phase | Approved |
| Structure Type | MOL |
| InChI Key | WEXRUCMBJFQVBZ-UHFFFAOYSA-N |
| Therapeutic | ✓ Yes |
4
Targets
9
Activities
2
Assay Types
4
PK Parameters
20
Publications
5
Known Names
5
Indications
1
Mechanisms
Molecular Properties
226.3
MW (Da)
1.18
ALogP
3
HBA
2
HBD
75.3
PSA (Ų)
0.71
QED
0
Ro5 Violations
4
Rot. Bonds
Drug Information
| Molecule Type | Small molecule |
| First Approval | 1973 |
| Availability | Withdrawn |
| Chirality | Racemic |
Mechanism of Action
| Mechanism | Action Type | Target | Direct | Efficacy |
|---|---|---|---|---|
| GABA-A receptor; anion channel positive allosteric modulator | POSITIVE ALLOSTERIC MODULATOR | GABA-A receptor; anion channel | ✓ | ✓ |
Indications
Sleep Initiation and Maintenance Disorders Brain Injuries Status Epilepticus Heart Diseases Substance-Related Disorders
ATC Classification
N05CA01
pentobarbital
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS
Drug Warnings
Withdrawn
drug misuse
Fatal intoxications and abuse
Withdrawn
drug misuse
Self-Poisonings
Activity Summary
IC50 7 meas. best 5.77
EC50 2 meas. best 4.3
Target Activity Profile
| Target | Type | Best pChEMBL | Mean pChEMBL | Best (nM) | # Data |
|---|---|---|---|---|---|
| GABA-A receptor; anion channel CHEMBL1907607 | IC50 | 5.77 | 5.085 | 1700.0 | 2 |
| GABA A receptor alpha-2/beta-2/gamma-2 CHEMBL2111413 | EC50 | 4.3 | 4.3 | 50000.0 | 1 |
| Xenopus laevis CHEMBL613478 | EC50 | 4.19 | 4.19 | 65000.0 | 1 |
| Gamma-aminobutyric acid receptor subunit beta-3 CHEMBL1847 | IC50 | 4.06 | 4.06 | 88000.0 | 1 |
Pharmacokinetic Data
| Parameter | Value | Units | Species |
|---|---|---|---|
| CL | 0.47 | mL.min-1.kg-1 | Homo sapiens |
| Fu | 0.39 | - | Homo sapiens |
| MRT | 32.0 | hr | Homo sapiens |
| T1/2 | 22.0 | hr | Homo sapiens |
Activity Data Samples
Top measurements by pChEMBL value
| Target | Type | Rel. | Value | Units | pChEMBL | Assay | PubMed |
|---|---|---|---|---|---|---|---|
| GABA-A receptor; anion channel | IC50 | = | 1700.0 | nM | 5.77 | Ability to allosterically modulate the binding of [35S]TBPS to gamma-aminobutyri... | 9016329 |
| GABA-A receptor; anion channel | IC50 | = | 40000.0 | nM | 4.4 | Inhibition of [35S]TBPS binding to GABA-A receptor in rat cerebral cortex. | 9599235 |
| GABA A receptor alpha-2/beta-2/gamma-2 | EC50 | = | 50000.0 | nM | 4.3 | Effective concentration against GABA-evoked chloride currents mediated by human ... | 15801854 |
| Xenopus laevis | EC50 | = | 65000.0 | nM | 4.19 | Anesthetic activity in Xenopus laevis tadpoles assessed as loss of of righting r... | 22734650 |
| Gamma-aminobutyric acid receptor subunit beta-3 | IC50 | = | 88000.0 | nM | 4.06 | Displacement of [3H]R-(-)-14 from human FLAG-tagged beta3 GABA A receptor expres... | 22734650 |
Literature References
| PubMed | DOI | Target Context | # Activities |
|---|---|---|---|
| - | 10.6019/CHEMBL3885881 | Rattus norvegicus | 408 |
| 22194678 | 10.1371/journal.pcbi.1002310 | Hepatotoxicity | 14 |
| 7154009 | 10.1021/jm00354a017 | Canis familiaris | 6 |
| 3599019 | 10.1021/jm00390a002 | No relevant target | 6 |
| 1977910 | 10.1021/jm00173a012 | Monkey | 6 |
| 18426954 | 10.1124/dmd.108.020479 | ADMET | 4 |
| 37468498 | 10.1038/s41467-023-40064-9 | Alpha-1A adrenergic receptor | 3 |
| 20014752 | 10.1021/tx900326k | Hepatotoxicity | 3 |
| - | 10.6019/CHEMBL4651402 | SARS-CoV-2 | 2 |
| - | 10.6019/CHEMBL4495565 | SARS-CoV-2 | 2 |
| 22734650 | 10.1021/jm300631e | Gamma-aminobutyric acid receptor subunit alpha-1 | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Gamma-aminobutyric acid receptor subunit alpha-1 | 2 |
| 37468498 | 10.1038/s41467-023-40064-9 | Mu-type opioid receptor | 2 |
| - | 10.6019/CHEMBL4808148 | Histone deacetylase 6 | 2 |
| 15801854 | 10.1021/jm049120y | GABA A receptor alpha-2/beta-2/gamma-2 | 2 |
| 533876 | 10.1021/jm00197a005 | No relevant target | 2 |
| 22734650 | 10.1021/jm300631e | Gamma-aminobutyric acid receptor subunit beta-3 | 2 |
| 26948801 | 10.1016/j.drudis.2016.02.015 | Homo sapiens | 2 |
| 6864729 | 10.1021/jm00361a014 | No relevant target | 2 |
| 2579237 | 10.1021/jm00381a019 | Sodium channel alpha subunits; brain (Types I, II, III) | 2 |
Data from ChEMBL 36 via Core Engine